Dressing the furkids is totally all about me. It makes me happy to see them in their cute outfits! But functionally, there is a place for coats/rain gear/ect when you own a small breed like this. I see most dog owners w/at least a winter and rain jacket for their small dogs regardless if they dress them any other time.
I think the key to getting a dog to like wearing clothes (or tolerate it), is to make sure the clothes are comfy number one, and number two start when they are young for small periods of time. Give lots of treats while you are dressing them and while the outfit is on